CN110862338A - Preparation method and application of stachydrine ionic liquid - Google Patents

Preparation method and application of stachydrine ionic liquid Download PDF

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CN110862338A
CN110862338A CN201911149889.9A CN201911149889A CN110862338A CN 110862338 A CN110862338 A CN 110862338A CN 201911149889 A CN201911149889 A CN 201911149889A CN 110862338 A CN110862338 A CN 110862338A
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acid
stachydrine
ionic liquid
organic acid
solution
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张嘉恒
余明远
王岩
费玉清
闫修瑜
陈正件
张晃淳
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Zhuhai Zhongke Advanced Technology Research Institute Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters

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Abstract

The invention discloses a preparation method and application of stachydrine ionic liquid, and belongs to the technical field of materials. The method comprises the steps of dissolving stachydrine hydrochloride and organic acid by using solvents respectively, directly mixing the stachydrine hydrochloride solution with the organic acid solution after passing through ion exchange resin for neutralization reaction, and finally obtaining the stachydrine organic acid ionic liquid by a solvent removal process. The synthetic method has the advantages of simple process, environmental protection and easy popularization, the synthesized ionic liquid has high purity and is degradable, the problems of toxic residue and emission pollution of the traditional solvent are solved, and the synthetic method has application prospects in the fields of extraction, medicines, foods, cosmetics and the like.

Description

Preparation method and application of stachydrine ionic liquid
Technical Field
The invention belongs to the technical field of synthesis of biological ionic liquid, and relates to a preparation method and application of stachydrine organic acid ionic liquid.
Background
The stachydrine is one of main alkaloids of plants in motherwort (Leonurus Linn.) of Labiatae, and accounts for 0.09-1.01% of the total mass of the motherwort plants. Research shows that the stachydrine has the treatment effect on cardiovascular diseases besides gynecological diseases such as uterine bleeding, abnormal uterine contraction and the like, and can relieve the injury of hypoxia and reoxygenation on endothelial cells of umbilical veins of human beings, improve the aging of endothelial cells induced by high glucose, treat cardiac hypertrophy and other multiple effects caused by various reasons. In addition, stachydrine has effects of inhibiting inflammation and oxidative stress, and has certain antitumor activity. The commercially available product is low pH stachydrine hydrochloride, which is corrosive to tissues. On the other hand, to achieve the ideal therapeutic effect, the concentration of stachydrine hydrochloride in serum needs to be certain, and excessive chloride ion intake may cause diseases such as kidney injury and coronary heart disease (journal of mathematical and pharmacology, 2018,31(11): 12-14.; Anhui medicine, 2017(08): 35-37.). The tissue damage caused by too low pH can be avoided by neutralizing with alkali, but the secondary side effect caused by high chlorine and high sodium and potassium is potential. In addition, the amount of drug in the original form entering the blood circulation is reduced due to the first-pass effect, and the increase in the dose can increase the concentration of the effective drug in the serum, but also has the risk of potential drug poisoning.
By replacing chloride ions in stachydrine hydrochloride with organic acid radical anions, the stachydrine is prepared into ionic liquid which can be converted into a form with weaker intermolecular interaction and lower crystallinity or exist in a liquid form, so that the solubility of drug molecules is effectively increased, the percutaneous absorption effect of the drug is enhanced, and the purpose of efficiently and targeted delivering the drug is achieved (Journal of Pharmacy and Pharmacology,2019,71(4): 441-463.). Meanwhile, by introducing the functional organic acid, the compound can be compatible with stachydrine to obtain a novel preparation with multiple effects, so that the high bioavailability of the preparation at lower concentration is realized, and the effects of continuous administration and sustained release are achieved. In addition, as the form of the stachydrine is liquid, the raw materials are green and environment-friendly and can be biologically degraded, so that the application of the stachydrine in the aspects of novel solvents, extraction, electrolytes and the like is expanded, and the problem of toxic residue of the traditional solvents can be solved.
Disclosure of Invention
The invention aims to provide a preparation method of stachydrine ionic liquid, which solves the problems that the salt precipitated in the stachydrine ionic liquid prepared by a salting-out method and a precipitation method is difficult to separate, and the stachydrine is weak in alkalinity and easy to separate out by water separation.
In order to achieve the purpose, the technical scheme of the invention is as follows:
the invention provides a preparation method of stachydrine organic acid ionic liquid, which comprises the following steps: respectively dissolving stachydrine hydrochloride and organic acid in a solvent, then converting the aqueous solution of the stachydrine hydrochloride into an aqueous solution of stachydrine hydroxide by an ion exchange method, directly mixing the converted solution with an organic acid solution to obtain a mixed solution containing the stachydrine and the organic acid, and removing the solvent from the mixed solution to obtain the stachydrine organic acid ionic liquid for later use. Preferably, the molar ratio of the stachydrine hydrochloride to the organic acid is 1: 0.1-3.0.
The stachydrine organic acid ionic liquid has the following structure:
Figure BDA0002283247220000021
in the structure, X-represents organic acid radical anion.
The solvent can be one or more of water, methanol, acetonitrile, ethanol, isopropanol and n-butanol.
The organic acid is salicylic acid, acetylsalicylic acid, caproic acid, caprylic acid, capric acid, benzoic acid, oxalic acid, gluconic acid, butyric acid, suberic acid, citric acid, malic acid, tea acid, valeric acid, adipic acid, tartaric acid, succinic acid, gallic acid, lactic acid, formic acid, azelaic acid, acetic acid, vanillic acid, syringic acid, caffeic acid, nascent acid, tartaric acid, nonanoic acid, collagen acid, pulmonic acid, sebacylic acid, valine, isoleucine, leucine, benzoic acid, methionine, tryptophan, threonine, gamma-aminobutyric acid, aspartic acid, cysteine, proline, serine, tyrosine, phenylalanine, glycine, glutamic acid, alanine and glutamine.
The stachydrine organic acid ionic liquid is prepared by one step by an ion exchange method, and the preparation method comprises the following steps:
0.10mol of stachydrine hydrochloride and 0.01-0.30 mol of organic acid are respectively dissolved in a solvent to obtain a stachydrine solution and an organic acid solution. The stachydrine solution is then passed through a strongly basic anion exchange resin. And finally, directly adding the solution passing through the ion exchange resin into an organic acid solution for neutralization reaction, and then obtaining the stachydrine organic acid ionic liquid through a solvent removal process.
The mass ratio of the stachydrine to the strongly basic anion exchange resin is 1: 5-45; the frequency of the stachydrine hydrochloride aqueous solution passing through the ion exchange resin is 1-5, and the amount of distilled water leached by distilled water each time is 1-5 times of the column volume; the solvent removing step may be one of evaporation, distillation under reduced pressure, vacuum drying and spray drying. The solvent removing process method is characterized in that the temperatures of evaporation, reduced pressure distillation, vacuum drying and spray drying are all 10-100 ℃.
Further, the synthesis route of the stachydrine organic acid ionic liquid can be that the stachydrine and one or more organic acids are mixed for reaction, and the stachydrine organic acid ionic liquid is prepared into one or a mixture state of liquid, solid and solution by designing the composition of organic acid anions.
The ionic liquid is used as an additive for food, medicines, daily chemical products and the like, and the content of the ionic liquid used as the additive is properly added according to the toxicity of anions and the use scene.
The ionic liquid is used as an extracting agent to extract the cash crops;
preferably, the mass ratio of the ionic liquid as a solvent to the extract to be extracted is 10: 0.3-5;
preferably, the mass ratio of the ionic liquid as a solvent to other solvents is 1: 0-0.5, and the other solvents can be one or a mixture of water, methanol, acetonitrile, ethanol, isopropanol and n-butanol;
preferably, the extraction temperature of the ionic liquid as a solvent is 0-80 ℃.
The invention has the advantages that:
the raw material reagent selected by the invention is green and environment-friendly, and is biodegradable, the preparation method is simple, efficient and easy to use, and the obtained stachydrine ionic liquid has high purity. The composition can be designed into a prescription with multiple efficacies as a medicine, and has the characteristics of good percutaneous absorption effect and targeted sustained-release administration; the solvent has the characteristics of good extraction effect, biodegradability and no toxic residue; the additive used as daily chemical product has the characteristics of hemostasis and anti-inflammation, anti-inflammation and allergy relief and small toxic and side effect.
Drawings
FIG. 1 is the NMR hydrogen spectrum of stachydrine-acetic acid ionic liquid synthesized in example 3 according to the invention;
FIG. 2 is a TGA spectrum of the stachydrine-acetic acid ionic liquid synthesized in example 3 according to the invention;
FIG. 3 is a graph showing the antioxidant effect of the stachydrine-acetic acid ionic liquid synthesized in example 7 according to the present invention.
Detailed Description
The invention is explained in more detail below with reference to the figures and examples, without limiting the scope of the invention.
Example 1
0.10mol of stachydrine hydrochloride and 0.15mol of salicylic acid were weighed out and dissolved in 100mL of distilled water, respectively, and then the stachydrine hydrochloride solution was passed through a chromatography column containing 800g of a pretreated strongly basic anion exchange resin, and the solution was passed through the chromatography column at a flow rate of 20 m/h. And mixing the solution after passing with a salicylic acid solution, and performing vacuum drying on the mixed solution for 48 hours under the conditions of 0.1mPa and 60 ℃ to obtain the stachydrine-salicylic acid ionic liquid [ Sta ] [ Sal ].
Example 2
0.10mol of stachydrine hydrochloride and 0.10mol of azelaic acid are weighed out and dissolved in 100mL of distilled water acetonitrile respectively, and then the stachydrine hydrochloride solution is passed through a chromatographic column filled with 100g of pretreated strongly basic anion exchange resin, and the solution is passed through the chromatographic column at a flow rate of 15 m/h. Mixing the solution after passing with azelaic acid solution, evaporating the mixed solution at 60 deg.C until the weight does not change any more, and obtaining stachydrine-azelaic acid ionic liquid [ Sta ] [ Aze ].
Example 3
0.10mol of stachydrine hydrochloride and 0.30mol of acetic acid were weighed out and dissolved in 100mL of ethanol, respectively, and then the stachydrine hydrochloride solution was passed through a chromatography column containing 350g of a pretreated strongly basic anion exchange resin, and the solution was passed through the chromatography column at a flow rate of 10 m/h. And mixing the solution after passing with an acetic acid solution, and performing rotary evaporation on the mixed solution at the temperature of 30 ℃ until no condensate is generated, thereby finally obtaining the stachydrine-acetic acid ionic liquid [ Sta ] [ Ace ].
Example 4
0.10mol of stachydrine hydrochloride and 0.05mol of protocatechuic acid were weighed out and dissolved in 100mL of n-butanol, respectively, and then the stachydrine hydrochloride solution was passed through a chromatography column containing 600g of a pretreated strongly basic anion exchange resin, and the solution was passed through the chromatography column at a flow rate of 20 m/h. And mixing the solution after passing with a protocatechuic acid solution, and performing rotary evaporation on the mixed solution at 65 ℃ until no condensate is generated, thus obtaining the stachydrine-protocatechuic acid ionic liquid [ Sta ] [ Pro ].
Example 5
0.10mol of stachydrine hydrochloride and 0.20mol of gluconic acid are weighed out and dissolved in 100mL of isopropanol respectively, and then the stachydrine hydrochloride solution is passed through a chromatographic column filled with 400g of pretreated strongly basic anion exchange resin, and the solution is passed through the chromatographic column at a flow rate of 15 m/h. And mixing the solution after passing with a gluconic acid solution, evaporating and drying the mixed solution at 50 ℃ until the quality is unchanged, and then drying in vacuum at 50 ℃ for 24 hours to obtain the stachydrine-gluconic acid ionic liquid [ Sta ] [ Glu ].
Example 6
0.10mol of stachydrine hydrochloride and 0.10mol of o-acetylsalicylic acid were weighed out and dissolved in 100mL of distilled water, respectively, and then the stachydrine hydrochloride solution was passed through a chromatography column containing 500g of a pretreated strongly basic anion exchange resin, and the solution was passed through the chromatography column at a flow rate of 10 m/h. And mixing the solution after passing with an o-acetylsalicylic acid solution, and performing rotary evaporation drying on the mixed solution at the temperature of 60 ℃ until no condensate is generated to finally obtain the stachydrine-o-acetylsalicylic acid ionic liquid [ Sta ] [ Asp ].
Example 7
The extraction and application of the moxa polyphenol by using the stachydrine organic acid ionic liquid as an extractant comprises the following steps:
(1) weighing the stachydrine acetic acid ionic liquid prepared in the embodiment 3, uniformly mixing the stachydrine acetic acid ionic liquid and ethanol according to the mass ratio of 10:3, putting the obtained mixed liquid and moxa into a mixing instrument, oscillating for 10min, and then extracting for 20min in an extractor under the ultrasonic environment of 50kHz, wherein the extraction temperature is 40 ℃.
(2) Centrifuging and coating the extracting solution obtained in the step (1) to obtain a brown clear liquid, and adding benzalkonium chloride to obtain the moxa polyphenol extracting solution.
(3) Mixing the extracting solution obtained in the step (2), glycerol and capsaicin according to the mass ratio of 3:100:0.01, adjusting the pH to about 7 by using triethanolamine, stirring for 20min by using ultrasound to obtain light yellow transparent liquid, and bottling for later use.
The oxidation resistance of the extractive solution of moxa based on the ionic liquid obtained in example 7 and the mixed solution of methanol and water was compared, and the results show that the removal effect of the free radicals by the stachydrine acetic acid ionic liquid and the conventional solvent is similar, and the specific effect is shown in fig. 3.
The stachydrine organic acid ionic liquid is used as an additive for food, medicines, daily chemical products and the like, and the content of the stachydrine organic acid ionic liquid used as the additive is properly added according to anion toxicity and use scenes. For the stachydrine, the LD50 or MTD (maximum tolerance) of the stachydrine hydrochloride is more than 5000mg kg < -1 >, and no animal death occurs in the toxicity test process, so that the method meets the national standard for low-toxicity or non-toxic substances. For the anion, if the anion is irritant, such as acetylsalicylic acid is used as the anion, the ionic liquid rat toxicity test LD50 is about 200 mg/kg, which is that the toxic substance should be used in proper amount; and if the substance is a low-irritation substance, such as valine, the toxicity data LD50 of the ionic liquid is more than 5000mg/kg, and the ionic liquid belongs to a low-toxicity or non-toxicity substance and can be used freely.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing examples, it will be apparent to one skilled in the art that various changes in the form and details of the foregoing embodiments may be made, and equivalents may be substituted for elements thereof without departing from the spirit and scope of the invention as hereinafter claimed.

Claims (10)

1. A preparation method of stachydrine organic acid ionic liquid is characterized by comprising the following steps: the method comprises the following steps: respectively dissolving stachydrine hydrochloride and organic acid in a solvent, then converting the stachydrine hydrochloride solution into a stachydrine hydroxide solution by an ion exchange method, directly mixing the converted solution with an organic acid solution to obtain a mixed solution containing the stachydrine and the organic acid, and removing the solvent from the mixed solution to obtain the stachydrine organic acid ionic liquid for later use.
2. The method for preparing stachydrine organic acid ionic liquid according to claim 1, wherein the stachydrine organic acid ionic liquid has the following structure:
Figure FDA0002283247210000011
in the structure, X-represents organic acid radical anion.
3. The method for preparing stachydrine organic acid ionic liquid as claimed in claim 1, wherein the solvent can be one or more of water, methanol, acetonitrile, ethanol, isopropanol and n-butanol.
4. The method for preparing stachydrine organic acid ionic liquid according to claim 1, the organic acid is salicylic acid, acetylsalicylic acid, caproic acid, caprylic acid, capric acid, benzoic acid, oxalic acid, gluconic acid, butyric acid, suberic acid, citric acid, malic acid, tea acid, valeric acid, adipic acid, tartaric acid, succinic acid, gallic acid, lactic acid, formic acid, azelaic acid, acetic acid, vanillic acid, syringic acid, caffeic acid, nascent acid, tartaric acid, nonanoic acid, collagen acid, pulmonic acid, sebacylic acid, valine, isoleucine, leucine, benzoic acid, methionine, tryptophan, threonine, gamma-aminobutyric acid, aspartic acid, cysteine, proline, serine, tyrosine, phenylalanine, glycine, glutamic acid, alanine and glutamine.
5. The method for preparing stachydrine organic acid ionic liquid as claimed in claim 1, wherein the molar ratio of the stachydrine hydrochloride to the organic acid is 1: 0.1-3.0.
6. The method for preparing the stachydrine organic acid ionic liquid according to claim 1, wherein the solvent removing step of the mixed solution of the stachydrine and the organic acid comprises evaporation, reduced pressure distillation, vacuum drying or spray drying, and the evaporation, reduced pressure distillation, vacuum drying and spray drying are carried out at the temperature of 10-100 ℃.
7. The method for preparing the stachydrine organic acid ionic liquid as claimed in claim 1, wherein the synthesis route of the stachydrine organic acid ionic liquid can be that the stachydrine and one or more organic acids are mixed and reacted, and the composition of organic acid anions is designed to prepare the stachydrine organic acid ionic liquid into one or a mixture of liquid, solid and solution.
8. The use of the stachydrine organic acid ionic liquid as an additive according to claim 1, wherein the ionic liquid is used as an additive for food, medicine, daily chemical products and the like, and the content of the ionic liquid as the additive is properly added according to anion toxicity and use scenes.
9. The use of stachydrine organic acid ionic liquid as an extractant according to claim 1, characterized in that the ionic liquid is used as an extractant for extracting commercial crops.
10. The application of the stachydrine organic acid ionic liquid as an extracting agent according to claim 9, wherein the mass ratio of the ionic liquid serving as a solvent to be extracted is 10: 0.3-5; when the ionic liquid is used as a solvent, the mass ratio of the ionic liquid to other solvents is 1: 0-0.5; when the ionic liquid is used as a solvent, the extraction temperature is 0-80 ℃; the other solvent may be a mixture of one or more of water, methanol, acetonitrile, ethanol, isopropanol, n-butanol.
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CN112915044A (en) * 2021-02-07 2021-06-08 珠海中科先进技术研究院有限公司 Composite hydrogel material and preparation method and application thereof
CN115073346A (en) * 2022-06-30 2022-09-20 中科萱嘉医养(珠海)健康科技有限公司 Stachydrine ionic liquid and preparation method and application thereof

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Publication number Priority date Publication date Assignee Title
CN111481582A (en) * 2020-04-13 2020-08-04 珠海中科先进技术研究院有限公司 Method for extracting wormwood polyphenol from EDTA (ethylene diamine tetraacetic acid) alcamines ionic liquid
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CN111529696B (en) * 2020-06-19 2021-02-19 广东天普生化医药股份有限公司 Application of ulinastatin in preparing medicine for preventing nasopharyngeal cancer metastasis
CN112225777A (en) * 2020-09-16 2021-01-15 珠海中科先进技术研究院有限公司 Ionic liquid and method for extracting cod roe protein by using same
CN112225777B (en) * 2020-09-16 2022-05-20 珠海中科先进技术研究院有限公司 Ionic liquid and method for extracting cod roe protein by using same
CN112915044A (en) * 2021-02-07 2021-06-08 珠海中科先进技术研究院有限公司 Composite hydrogel material and preparation method and application thereof
CN115073346A (en) * 2022-06-30 2022-09-20 中科萱嘉医养(珠海)健康科技有限公司 Stachydrine ionic liquid and preparation method and application thereof
CN115073346B (en) * 2022-06-30 2024-03-19 中科萱嘉医养(珠海)健康科技有限公司 Stachydrine ionic liquid and preparation method and application thereof

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Application publication date: 20200306